Boron tribromide → HCID 57722970, compound

HRID 1987030Notes

Reaction equation

HRID 1987030 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17]2[C:12](=[C:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[CH:14]=[C:15]([O:18]C)[CH:16]=2)[CH:11]=[CH:10][C:9]1=[O:27].B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17]2[C:12](=[C:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[CH:14]=[C:15]([OH:18])[CH:16]=2)[CH:11]=[CH:10][C:9]1=[O:27]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57722990HCID 57722990, compound

Product 1

HCID 57722970HCID 57722970, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,5-bis(2-chlorophenyl)-7-methoxy-2(1H)-quinolinone (0.863 g, 2.178 mmol) was dissolved in dichloromethane (40 ml) and 1M boron tribromide in dichloromethane (12 ml) added slowly under nitrogen. The solution was stirred at 21° for 4 h, then quenched carefully with methanol (3 ml) and ice (25 g). The mixture was passed through a hydrophobic frit, and the aqueous phase further extracted with dichloromethane (20 ml), and passed through a hydrophobic frit. The dichloromethane extracts were combined and evaporated in vacuo to afford the title compound as a dark solid (0.784 g, 94%).

Workup

  1. customquenched carefully with methanol (3 ml) and ice (25 g)
  2. extractionthe aqueous phase further extracted with dichloromethane (20 ml)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-e657c8909adf4df782d0279b00c99c6a
Source dataset
uspto-grants-2009_06
Patent number
US07550480B2

Reaction notes

Loading…